What a Nice Surprise

"So does that mean you are declining my invitation?"

I didn't want to be rude, so I said, "Of course not. I would be happy to have dinner with you."

"Wonderful. I will pick the place. Shall we meet in the lobby again? Same time?"

"Sounds good." I had plenty of work to do, so I pushed dinner out of my mind. I attended a few other panel discussions held by a variety of colleagues, and headed back to the hotel just in time to meet Helen. When I walked into the lobby, she was already waiting.

"Here I was waiting for you to get off the elevator. Were you at the symposium all day?"

"I sure was."

"Would you prefer that we eat later? Are you still good to go?"

"Sure. What have you decided?"

Helen told me it was a surprise that she would be driving. I noticed that she had changed her clothes again. She looked wonderful in a dark red sweater dress, leggings, and boots. She had legs that were a mile long, and they were nice and firm. We pulled into a shopping mall area, and she could tell that I looked a bit confused.

"The guy at the front desk said this is the best Italian place in the city. If it sucks, we blame him."

I laughed and agreed to give it a shot. When we walked in there were no more than six tables. The ambiance was romantic. Tables had candles and white covers. The maitre de seated us, and we both ordered a glass of wine. "Wow. This place is kind of fancy. I wasn't expecting this when we pulled up."

"Me either," Helen began, "but I hope we can enjoy it."

And we did. We ordered appetizers and snacked on those while we talked and drank wine. We had a second glass of wine during diner and then a third. I could not believe all that we had in common ranging from books to movies to career choices. She even loved dogs as much as I did. It was nearing ten o'clock when she pointed out that we should be going.

"James, would you mind joining me for a nightcap? Just two friends finishing up a wonderful night?"

"Sure, why not." I wasn't sure if that was the wine talking or James junior, but either way I wanted to spend more time with this wonderful woman. When we arrived back at the hotel, we walked to her room. She opened the mini fridge and read off my choices. I selected gin and tonic. She poured some into a plastic cup and we clinked. "To new friends," I said.

That was when Helen stepped over and kissed me deeply. Her lips were so full and warm. Her tongue was cool and tasted of gin. Then she asked, "James, could we be more than friends for just a moment?"

"Mmmm...I would like that..." I set my cup down and kissed her deeply again. This time my tongue entered her mouth, and I caressed her left breast. While she had some sort of padded bra, I could feel her nipple get erect under my touch. We continued to kiss deeply until she stepped back. I was about to get pissed because I thought she was playing me again, but she surprised me when she lifted her off her dress. Her beautiful breasts filled out her bra. Her stomach was flat and her legs were crossed as if she were shy.

"James," she began, "I want you to touch me, but you won't want me."

I took a step forward. "Helen, I do want you." She uncrossed her legs and about shit my pants. Inside of her cute panties sprang a cock. "What the fuck? You're a man?"

Helen began to tear up. "No, I am not a man. I mean I was born a man, but this is all I have left of that life. This is why I stopped you yesterday. I knew you would be repulsed."

"Shocked, yes? Repulsed, no."

"You had no idea?" It was a question not a statement.

"Helen, you are beautiful. Why would I have any idea? I apologize for the "what the fuck" comment. That was rude and abrasive."

Helen lifted up her hair and turned to the side. "James, look. I have an Adam's apple." She dropped her hair and lifted up her hands. "These are not small, dainty hands."

"Well all be son-of-a-bitch," I replied in disbelief. I sat down in a chair. Helen went to put her dress back on. Her erection was gone and so was mine. I shocked myself when I said, "No, don't cover yourself."

"Aren't you repulsed? You're not gay. Why aren't you running out of here?"

"Nope. I'm not gay. But you're not a man. Remember..." I smiled at her trying to reassure her that I was not some sort of asshole.

"So can we still be friends?" Helen asked, almost timid-like. Here she was sitting before me damn near naked, and I didn't mean just her clothes.

I wasn't sure what was happening, but I got up and sat next to her on the bed. I put my hand on her leg, and said, "Of course we can be friends." And then I kissed her deeply.

After several seconds of heavy kissing, she pulled back and looked at me. Her eyebrows were arched up and she tilted her head to the side a little bit. "Are you sure about this?"

"Nope. But I am sure that I like you." That was all that she needed to hear. She leaned in and kissed me again. This time I wrapped my arms around her chest and pulled her close. We fell back on the bed and continued to make out. She unbuttoned my shirt while she kissed my neck, chin, and cheeks. Once the final button was undone, I pulled it off and threw it on the floor. I reached around and unclasped her bra. Her breasts- clearly not real- were firm and perky. The nipples were perfect. They looked like pink erasers sitting on top of dark areolas.

"Does it feel good if I suck on your nipples?" I asked. I had no idea what I was doing, but I hoped asking wasn't offensive.

"Of course it feels good," she said breathlessly. I moved my face down to her mounds and suckled. Her skin was so soft, and I loved hearing moans as I nursed each breast wanting more. At one point, I looked down and her cock was bulging in her red panties. A typical man might have said that it confusing or gross to see a cock, but I was incredibly turned on. As I suckled her breasts, I moved my hand down and rubbed her erection through her panties.

"James?" Helen stopped and looked at me. "Are you sure? I mean we can keep this simple. Just focus on the goods up top?"

"Helen. I want to be with you." She kissed me again, and I pulled out her erection. I could feel the precum on the tip of her head. As a man, I knew exactly what to do with that; so I smeared it around her head and began to stroke up and down. Helen began to moan and move her hips back and forth. I continued to jack her cock. I spit in my hand and placed it back on her erection.

"James...you gotta stop...or I will cum...it's been a really really long time since anyone touched me. I won't last long."

"That's okay. We have all night, and I'm a very patient man. I moved my mouth back to her breast and nibbled on her nipple. Helen let out a grunt and then a heavy sigh. I felt the cum land on the back of my hand. I guess for my first hand job, I didn't do too bad...

"That was amazing," Helen began. "I can't believe you did that. I'm embarrassed. I knew I wouldn't last long." I smiled at her and retreated into the bathroom. I washed my hands and brought her a warm towel to clean up with. "It's your turn now. Are you ready for me, James?"

"I am."

"Lay back on the bed." I followed her instructions and propped my head up on a pillow. Helen started with my mouth and kissed down my neck. She ran her hands through my chest hair stopping for a moment to play with nipples. She then undid my belt, unbuttoned my pants, and pulled them down. She rubbed my erection with her hands. Then she would rub my balls. Then she would rub my inner thighs. She repeated this pattern for several minutes. "James, would you like me to take your manhood into my mouth?"

"Yes."

"Say it."

"I want you to take my manhood into my mouth."

"No...James...tell me what you really want. What is it that you must feel right now..." Helen said this in almost a pur. She was rubbing my cock while she talked, but she never broke eye contact with me.

"Helen, I want you to suck my cock. I want your lips around my shaft. I want you to milk me dry. Your lips are so full and luscious. I want to see them wrapped around my cock."

"Much better, James." Helen removed my briefs and lowered her mouth to my erection. I have a rather large, bulbous head that almost turns purple when I am really horny. She placed just the head in her mouth and swirled her tongue around it. God it felt good. Then she moved down...all the way down until I could feel my head touch the back of her throat. I do not have a large dick by any means, but fuck...I am not small either. It did not matter to Helen though. She took my entire member, moving up and down with her mouth and her lips. As her mouth went up, her hand followed, so my cock was never left untouched. I loved hearing the PLOP sound when my head would come out of her mouth. She varied the sucking from firm to light. Fast to slow.

"How does that feel, baby?"

"So...fucking...good..." I replied. I continued to watch her fuck me with her mouth.

"James, I want you to hold my head. Just like this..." she put both of my hands on the side of her head. "I want you to fuck my mouth until you feel the orgasm building in your balls. Then stop. I will finish you off.

I did just that. I placed both of my hands on her head and moved my hips back and forth fucking her mouth as if it were dripping wet pussy aching to feel my manliness. She held her mouth in an O shape making sure that I did not hit her teeth. The underside of my cock drug against her tongue, and I knew I would not last long.

"I'm close..." I barely got the words out of my mouth when Helen took over. I dropped my hands, and she began rubbing my balls while deep throating me. She did not move quickly- but slowly with intense sucking. And that is when it hit...wave after wave...And she took it all. I have no idea how much I came, but it had to be a lot. She swallowed every stop and then licked me clean. I was panting when I said, "That was the most amazing blow job...thank you."

She sat up and laughed. "Well...I do know a thing or two about blow jobs." She brushed the hair out of her face and looked at me. "What?"

"Thank you, James. For this...for not being a total asshole about what I am...or rather who I am."

"Come here," Helen crawled up the bed and laid in the crook of my arm. I kissed her softly. "I like you...I don't know what else to say...but I like you..."

"I like you too..." She gave me a soft kiss on the tip of my nose.

"Hey that tickles..." I kissed her back on the tip of her nose.

"You're right it does tickle..." Then she kissed me softly on the lips. I returned the kiss. She pulled away and looked at me. For a moment we said nothing. I leaned in and kissed her again, but this time my desire grew. Something changed between us. We became animals. She climbed on top of me and kissed me with intense passion. She fed me her tongue. She bit my lips. Her breathing increased. I felt her erection on my stomach. At one point she reached down to adjust it, which caused my dick to stir. I was not a gay man, but this moment was incredibly erotic.

"Would you rub your cock on mine?" I asked her.

"Really?"

"Mmmm yes...what does that feel like? I want to know."

Helen leaned forward, so her penis was laying on top of my penis. She then took both of us into her hand and began stroking...it was as if she was giving us both a hand job at the same time. I could feel her hand on one side and her cock on the other side. The precum literally leaked out of my head. I could not control it. She used her precum and mine as lube and continued to stroke us at the same time. I could not believe my recovery time was almost immediate; I was rock solid. Helen then stopped stroking and leaned forward to kiss me more. She was now grinding her cock into mine. We were moving up and down when she moved forward a bit too much, and my head hit the entrance to her ass.

"Ooof. I'm sorry. I'm getting carried away," she said breathlessly.

"Don't be. I want to be inside of you."

"Seriously?"

"Yes...I want to know what your tight ass feels like wrapped around my cock." Helen's eyes bulged out her head. She spit on her hand and applied it to my erection. She leaned up and slowly slid down on my cock. She was so tight. Her ass did not feel like a pussy. A woman is wet, and there is some give when my cock is inside of vagina. This however was a totally different feeling. I could feel the friction without proper lube, and it was tight- almost vice grip tight.

"Does this feel good to you, James? Do you like being in my ass?"

"Yes baby! Let me fuck your tight ass. Or is this your pussy, Helen?"

Helen's smiled radiated when she said, "Fuck my pussy, James. I want you to impregnate me with your seed. Fuck me until I feel your semen fill me. Fill my womb." Holy hell...I was not ready for that level of hotness. I lost all control. I grabbed Helen's ass as she leaned forward, and I fucked her with intensity. The precum continued to leak out of me, which was perfect because I needed the lubrication.

"Baby, I'm gonna cum in your pussy if we keep this up..." I was so out of breath.

"Give me your seed, James..." I bucked my hips wildly. The orgasm built up in my balls, and I exploded into her ass...no...her pussy. Helen's pussy. As I slowed down my tempo, Helen leaned back. My cock was not soft, so I could feel it still pushing on her prostate.

"Does that hurt?" I asked?

"No...watch..." Helen just moved her hips slowly. Apparently my large head was rubbing her prostate in the right place. She took her right hand and rubbed just the head of her cock. She continued to almost sway her hips back and forth. Her eyes were closed and her lips tightened just slightly. I could feel her ass grip my shrinking cock, and then she grunted...spurt...spurt... two large ropes of cum landed on my chest. Helen opened her eyes, and started laughing. "That was...fucking amazing!! Oh my god! Thank you!" She leaned forward and put both of my cheeks in her hands and kissed me.

When she got off me, she took the washcloth in the bathroom to clean up. When she returned she took the warm towel and cleaned me off. I let out a giant yawn. It was after midnight.

Helen stood at the foot of the bed completely naked. Her limp cock hanging to the side just as my limp cock was hanging to the side. I put my hands behind my head. For a moment we just stared at each other's deflated dicks.

"Are you checking out my dick?" I joked. "You're totally sizing it up, aren't you?"

Helen smiled and said, "Hmmm...maybe."

"I'm tired. I'm an old man. You took advantage of me."

Helen put her hands on her hips, "Oh really? Did I?"

"Yep. Now you have to deal with my snoring. Get over here."

Helen tossed the washrag into the bathroom, and we crawled under the sheets. I was not sure what I was getting myself into, but damn it was hot.